2,6-Dibromopyridine → HCID 66171035, compound

HRID 885910Notes

Reaction equation

HRID 885910 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[NH2:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Br:8][C:4]1[N:3]=[C:2]([NH:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 735613-Amino-1,2-propanediolHCID 81531Diisopropylethylamine

Product 1

HCID 66171035HCID 66171035, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 2,6-dibromopyridine (0.76 g, 3.20 mmol), 1-amino-2,3-dihydroxypropane (0.29 g, 3.20 mmol) and DIPEA (0.56 mL, 3.24 mmol) in toluene (3.2 mL) was heated to 160° C. under microwave irradiation in a sealed tube for 2 h, and then concentrated in vacuo. Water (5 mL) was added, the mixture sonicated for 10 minutes, and then filtered through Celite®. The filtrate was concentrated in vacuo to yield the title compound (0.239 g, 30%) as a white solid that was used without further purification. δH (DMSO-d6) 7.29-7.18 (1H, m), 6.92-6.79 (1H, m), 6.61 (1H, d, J 7.3 Hz), 6.51 (1H, d, J 8.3 Hz), 4.79 (1H, d, J 4.9 Hz), 4.58 (1H, t, J 5.8 Hz), 3.65-3.54 (1H, m), 3.15-3.04 (1H, m). Exchangeable protons were not observed. LCMS (ES+) 247.0 and 249.0 (1:1 ratio) (M+H)+, RT 2.07 minutes (Method 1).

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater (5 mL) was added
  3. customthe mixture sonicated for 10 minutes
  4. filtrationfiltered through Celite®
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d76871b23e864b74b4e2f8e58b1527bc
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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